The Ledger

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Disclosure
Zuora CIO Chakkarapani refuses to pay vendors for enterprise POCs
“I would never pay because we need some skin in the game from the vendor who's supporting us.”
Karthik Chakkarapani Nov 28, 2025 ▶ 8:09 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Insight
SaaS will become merely an execution layer beneath autonomous AI agents
“SaaS is becoming more of an execution layer, not an intelligent layer. Now the intelligent layer is moving more towards the AI agents, where it is more autonomous in nature. Where, ah, where, when employees interact with it, they don't interact with the SaaS a…”
Karthik Chakkarapani Jul 11, 2025 ▶ 7:22 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Assertion Not checkable as stated
Zuora CIO: Atomicwork's AI agent resolves up to 50% of service requests
“Almost 40 to 50% of the employee incidents and requests were addressed by the AI agent.”
Karthik Chakkarapani Jul 11, 2025 ▶ 19:37 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Insight
Chakkarapani: Enterprise Buyers Evaluate Startup Team Rapport Beyond Product Viability
“Because if it is an established company, we don't have much of a say, we just test the value on the, of the product. But if it is a startup, this is almost like I treat them, I want to treat them as an extension of my team, like a thought partner. How do you g…”
Karthik Chakkarapani Nov 28, 2025 ▶ 14:50 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Insight
Chakkarapani: Enterprises should provide their own legal templates to startups
“So then we realized, you know what, rather than going back and forth for two, four weeks, and at the end of the cycle, they accepted 95% of our needs anyway, right? So I said, why are we doing this convoluted way? Why don't we just give them our document like …”
Karthik Chakkarapani Nov 28, 2025 ▶ 27:14 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora CIO: 80% of vendor discovery is outbound, only 10-20% inbound
“So inbound is very less, I would say, maybe 10 to 20% that we pay attention, but 80% is Outbound because it makes it easy for us.”
Karthik Chakkarapani Nov 28, 2025 ▶ 10:04 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Insight
Chakkarapani: Enterprises should bring business teams into initial vendor meetings alongside IT
“When we talk to the vendor, in the first meeting, we have the business teams in front of us. It's not like IT goes first and business comes. So we have a cross-functional team. That represents an AI, at least in the AI focus. And we keep them updated. We keep …”
Karthik Chakkarapani Nov 28, 2025 ▶ 38:08 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora Caps Startup Software Experimentation Phases at Four Weeks
“But once the terms and conditions are met, then we come with a four week plan. I don't go beyond four weeks, right, because there's no point in it.”
Karthik Chakkarapani Nov 28, 2025 ▶ 13:59 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Assertion Not checkable as stated
Chakkarapani: 80% of Employees at US-Based Startups Are Located Offshore
“I say majority of them, the companies, even though they're based in the US, 80% of their employee base is not in the US.”
Karthik Chakkarapani Nov 28, 2025 ▶ 56:26 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora CIO aims to close startup software purchases within six weeks
“So I like to go from the initial pitch to closing the sales in less than six weeks.”
Karthik Chakkarapani Jul 11, 2025 ▶ 24:29 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Disclosure
Zuora only signs one-year AI software contracts due to rapid obsolescence
“We are only signing one-year contracts, because the technology is changing so fast, and that's why I'm somewhere in the middle.”
Karthik Chakkarapani Jul 11, 2025 ▶ 20:01 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Opinion
Chakkarapani: Roughly one-third of the general workforce understands AI capabilities
“Talking to general population, I would say less, maybe one third of it understand what's possible in AI.”
Karthik Chakkarapani Jul 11, 2025 ▶ 30:49 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Disclosure
Zuora's Startup Vendor Evaluation Averages Two to Three Months to Contract
“So ideally I would say two to three months is average. For entire thing, and then the implementation begins, right? And ideally I want to see the value in the first three months, not like six months or nine months.”
Karthik Chakkarapani Nov 28, 2025 ▶ 17:40 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Assertion Not checkable as stated
Chakkarapani: Zuora evaluated 50+ AI apps in three months, deploying 12
“In the past three months we have almost put in almost, like, 50 plus applications through this process, and 12 of them have already gone into production.”
Karthik Chakkarapani Nov 28, 2025 ▶ 4:42 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Assertion Not checkable as stated
Zuora CIO: AI tools surge to 8–10 per quarter versus 2–3 traditional SaaS
“Even when we take a typical SaaS application, it takes anywhere from two to four weeks for legal compliance, and we were okay with that, because we don't roll out a new SaaS application every month. Maybe every quarter we may roll out like two or three, net ne…”
Karthik Chakkarapani Nov 28, 2025 ▶ 26:14 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Chakkarapani: One-fifth of Zuora's software stack is early-stage startups
“I would say almost like one fifth of our portfolio, or like zero to five years kind of in the startup ecosystem.”
Karthik Chakkarapani Nov 28, 2025 ▶ 29:45 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora decommissioned over 40 SaaS apps in two years
“So we decommissioned almost like, 40 plus apps in the last two years, and we consulted it with existing apps, and we moved into new apps, so now we have a very healthy set of apps, and the machine is not running, the engine is running now.”
Karthik Chakkarapani Nov 28, 2025 ▶ 6:55 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora CIO: Sales and marketing tools make up 30% to 35% of software spend
“Yeah, sales and marketing are the biggest spend. I would say it almost like, 30, 35% in that I don't have the numbers top of my head.”
Karthik Chakkarapani Nov 28, 2025 ▶ 22:55 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Assertion Not checkable as stated
Zuora CIO: Atomic Work's AI Agent Resolves 55% of Internal Incidents
“Now, as a matter of fact, we just saw the latest data, almost like 55% of our incidents and requests are, Been solved by the AI agent that Atomic Work provides.”
Karthik Chakkarapani Nov 28, 2025 ▶ 45:13 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Assertion Not checkable as stated
Chakkarapani: Truepeer cuts video production to four minutes across ten languages
“It takes four and a half hours to take one video end to end for one language. And with Truepeer, I can take, I can do one video in four minutes across 10 languages.”
Karthik Chakkarapani Nov 28, 2025 ▶ 21:23 3 Steps on How Large Companies Decide to Buy From a Startup or Not | CIO Karthik Chakkarapani
Disclosure
Zuora deployed Zoom AI Companion, Gemini, and NotebookLM company-wide
“In the last few months at Zora, we have enabled enterprise-wide AI tools. We rolled out Zoom AI Companion. We have rolled out Gemini. We have rolled out Notebook. All the common horizontal use cases, we have rolled it out.”
Karthik Chakkarapani Jul 11, 2025 ▶ 16:10 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
Disclosure
Zuora purchased 10 to 12 tools after evaluating 50 startup pitches
“I would say maybe 40 to 50 pitches. Personally, I go to many of these events, I use these events, so I get to get the elevator pitches and all those things. Some, sometimes it resonates, sometimes it doesn't resonate. And I would say what till date we have alm…”
Karthik Chakkarapani Jul 11, 2025 ▶ 24:00 What Startups Can Learn from a $1.7B Co. Chief Information Officer | Karthik Chakkarapani
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